(S)-2-tert-Butoxycarbonylamino-5-oxo-hexanoic acid ethyl ester → (S)-ethyl 5-methyl-3,4-dihydro-2H-pyrrole-2-carboxylate

HRID 1751674Notes

Reaction equation

HRID 1751674 reaction equation
C(OC([NH:8][C@@H:9]([CH2:15][CH2:16][C:17](=O)[CH3:18])[C:10]([O:12][CH2:13][CH3:14])=[O:11])=O)(C)(C)C>FC(F)(F)C(O)=O.ClCCl>[CH3:18][C:17]1[CH2:16][CH2:15][C@@H:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[N:8]=1

Participants

3

Reactant 1

HCID 58544329(S)-2-tert-Butoxycarbonylamino-5-oxo-hexanoic acid ethyl ester

Product 1

HCID 67682752(S)-ethyl 5-methyl-3,4-dihydro-2H-pyrrole-2-carboxylate

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

(S)-ethyl 2-(tert-butoxycarbonylamino)-5-oxohexanoate in a 1 L flask was treated with a trifluoro acetic acid/dichloromethane solution (1:1 mixture, 100 mL). Effervescence was observed and the mixture was allowed to stir for 4 hours at room temperature. After which time the volatiles were removed in vacuo to yield (S)-ethyl 5-methyl-3,4-dihydro-2H-pyrrole-2-carboxylate as an oil, and used directly in the following step.

Workup

  1. customAfter which time the volatiles were removed in vacuo

Sources & evidence

ORD record
ord-6be19fac10084c26b3be6b861f3064eb
Source dataset
uspto-grants-2015_10
Patent number
US09156823B2

Reaction notes

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